Diisopropylethylamine → 3-methyl-6-[2-(3-methyl-4-{[4-(1H-tetrazol-1-yl)phenyl]acetyl}piperazin-1-yl)ethyl]-3,4-dihydro-1H-isochromen-1-one

HRID 2173457Notes

Reaction equation

HRID 2173457 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=O)=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:40][CH:41]1[CH2:50][C:49]2[C:44](=[CH:45][CH:46]=[C:47]([CH2:51][CH2:52][N:53]3[CH2:58][CH2:57][NH:56][CH:55]([CH3:59])[CH2:54]3)[CH:48]=2)[C:43](=[O:60])[O:42]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:40][CH:41]1[CH2:50][C:49]2[C:44](=[CH:45][CH:46]=[C:47]([CH2:51][CH2:52][N:53]3[CH2:58][CH2:57][N:56]([C:13](=[O:15])[CH2:12][C:9]4[CH:8]=[CH:7][C:6]([N:1]5[CH:5]=[N:4][N:3]=[N:2]5)=[CH:11][CH:10]=4)[CH:55]([CH3:59])[CH2:54]3)[CH:48]=2)[C:43](=[O:60])[O:42]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 841658(4-Tetrazol-1-yl-phenyl)-acetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 772306783-methyl-6-[2-(3-methylpiperazin-1-yl)ethyl]-3,4-dihydro-1H-isochromen-1-one

Product 1

HCID 675180963-methyl-6-[2-(3-methyl-4-{[4-(1H-tetrazol-1-yl)phenyl]acetyl}piperazin-1-yl)ethyl]-3,4-dihydro-1H-isochromen-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of [4-(1H-tetrazol-1-yl)phenyl]acetic acid (101 mg, 0.49 mmol) in DCM (1271 μl) was treated with HATU (189 mg, 0.49 mmol) at room temp. After 5 minutes a solution of of 3-methyl-6-[2-(3-methylpiperazin-1-yl)ethyl]-3,4-dihydro-1H-isochromen-1-one (110 mg, 0.38 mmol) and DIEA (167 μl, 0.954 mmol) in DCM (1271 μl) was added and the reaction allowed to stir overnight at room temp. The reaction was quenched with water and SPE purification gives crude product which was purified via reverse phase HPLC (5-85% gradient elution ACN/H2O with 0.5% TFA) to obtain 3-methyl-6-[2-(3-methyl-4-{[4-(1H-tetrazol-1-yl)phenyl]acetyl}piperazin-1-yl)ethyl]-3,4-dihydro-1H-isochromen-1-one. LC-MS (IE, m/z): 475 [M+1]+.

Workup

  1. customThe reaction was quenched with water and SPE purification
  2. customgives crude product which
  3. customwas purified via reverse phase HPLC (5-85% gradient elution ACN/H2O with 0.5% TFA)

Sources & evidence

ORD record
ord-93e00251e0b542368e35adafc10bdd36
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

Loading…